Hydrochloric Acid → HCID 13723638, compound

HRID 1460634Notes

Reaction equation

HRID 1460634 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(N(CC)CC)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19].Cl>C(OCC)C>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:17](=[O:20])[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 13723638HCID 13723638, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 2,6-dimethylaniline (8.68 g, 0.0718 mole) and triethylamine (15.3 ml) in ethyl ether (250 ml) was cooled to +5° C. A solution of acryloyl chloride (6.47 g, 0.0716 mole) in ethyl ether (25 ml) was added dropwise with stirring over a 20 minute period. The solution was allowed to warm to room temperature and stirred for 72 hours. 10 Percent hydrochloric acid (150 ml) was added and the layers separated. The acid layer was extracted with ethyl acetate (150 ml), combined, washed with water (150 ml), dried over sodium sulfate, filtered and the solvents evaporated. The solid was taken up in hot ethyl acetate and recrystallized from hexane to yield the title compound, m.p. ca. 143.5°-145.0° C.

Workup

  1. temperaturewas cooled to +5° C
  2. stirringstirred for 72 hours
  3. customthe layers separated
  4. extractionThe acid layer was extracted with ethyl acetate (150 ml)
  5. washwashed with water (150 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents evaporated
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-4ffdd1c414d7415bb17c11c6d882f46d
Source dataset
uspto-grants-1991_12
Patent number
US05071876

Reaction notes

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